Asking for feedback can be a timing thing and can come about in snippets instead of all in one fell swoop...that'll overwhelm him, for sure!
After the details have been ironed out for the next outing...you can ask H in a light way, "Hey...I am glad we got to do this. It was fun getting this together. I am wondering how you would feel if you take on the next event yourself...I am sure you'll be very creative. What do you think?"
Sit back and listen. It is not R talk. It is allowing space for H to express his thoughts and it shows him that you're willing to let go of the "planner/planning" reins.
It is important to keep in mind:
-It is the moment/situation -It is the context -It is HOW you present information -It is how you react to H's thoughts